Guys out planting trees at the start of rainy season.  

Over the years, I’ve witnessed both newbie and seasoned investors get misled by various players in the real estate game, from wholesalers to contractors, realtors, property managers.

If you're open to mid term renting (we transition to this during our slower season), I'd also recommend speaking with the university and trying to see if you could try to be the source for their mid term housing.

It’s a short term rental started in Oct 2024 and earning during this off season is under $10K but cost segregation has nothing to do with rental income only depreciation of the property and with bonus depreciation being 60% this year I think it’s worth it.

The resources are endless here, but at some point, the messier it gets, the less seasoned investors are going to spend the time.

For a more general philosophy on hospitality, especially if you are going into the higher end STR space I would recommend Four Seasons: The Story of a Business Philosophy by Isadore Sharp about the founding and development of the Four Seasons brand. 

Engaging with seasoned investors and participating in discussions will expand your knowledge quickly.

I believe if I can present a bullet proof opportunity, I can find the funding.

The issue I see with your $500 allowance is that in some seasons they will definitely be seeing a big cost.

Hope everyone is having a wonderful holiday season!